My Story (Coming Out as Transgender)

I understand that to someone outside looking in, seeing another person raised as a (wo)man “suddenly deciding” to live as the other gender would seem like an artificial and arbitrary choice. However, for us that have lived it ourselves, it’s not that we just “decided” we preferred the other gender. It’s more that we always felt strangely uncomfortable with who we were and what was expected of us even if we didn’t quite understand the reason why. Some transgender people are lucky and realize the answer to their existential dread quickly, and this is the narrative that the media seems to push the most. That’s the archetype of a child who, from the get-go, refers to themselves as a girl when they were assigned to be a boy and vice versa. But there’s a lot of transgender people who maybe suspected the answer on some level, but weren’t allowed or able to explore the possibilities in order to be absolutely certain. In these cases, there may be multiple clues that go ignored, urges repressed, and confusion as the person goes along with the status quo out of fear or simply because it’s the path of least resistance. I’d like to share my own story in the hope that it aids others in understanding one such experience of transgenderism.

I offer my story as evidence of the fact that children should be allowed to explore themselves outside of any predetermined mold or gendered expectations. I believe if I had been granted that right, that my adolescence would have been far more pleasant and as a result, I’d be a more confident, successful person today. It’s my further wish that anyone on the fence, who might be considering transition but holding back, may use my story to better analyze their own situation.

Chapter 1: Repression

I was about 9 years old when I first knew something was off. I wasn’t a particularly happy little kid, I got cranky a lot and even looking back on pictures of myself as a toddler, I almost never smiled. I remember growing up and seeing that episode of Fairly Oddparents where Timmy becomes a girl and wishing more than anything that could happen to me. I even had dreams about it. There was another episode of a show called Lloyd in Space where a gender-neutral alien was made to “decide” which sex to adopt. Watching that, it hit me like a ton of bricks–if I could have chosen, I’d have chosen to be a girl. My reaction to both programs, seen just a few months apart, was instantaneous and powerful. There was no careful consideration of the pros and cons of being a girl versus being a boy, I just “knew.”

For awhile as a little kid I just assumed every guy thought about “what would it be like to be a girl” all the time. It seemed obvious to me that being a woman was better, so I just figured every other guy must have felt the same way deep down. As I grew up and had the courage to openly talk about these feelings with the men in my life, young and old, I soon realized I was alone in my thoughts. A lot of their reactions to my statements were complete bewilderment or even thinly veiled hostility. I also remember being very upset each time my girl friends at school or female cousins had girls-only sleepovers that I couldn’t attend. In each case, I’d confide in my parents, guy friends or male cousins about these feelings, and they’d all invariably say “what, you want to hang out with a bunch of girls playing dress up?!” I’d invariably think “…Um, yes. Is that bad..?” But because of the mockery, the virulent disgust of their responses, I knew I had to pretend to agree with them or risk getting ostracized or punished. Eventually, after enough of this, my natural assumption was that I was just some lone freak and these feelings were shameful, not to be shared with anyone.

As far back as I can remember, I would see myself in my mind’s eye as a girl and would model my actions or moods in line with “how would Clarissa Darling act in this situation?” or “how would XYZ girl-in-real-life-I-admire, carry herself in this company?” It was never a conscious choice to do so, I just automatically mirrored the women in my life in their mannerisms and poise. I still saw myself that way in my teen years, but I had to suppress the physical expressions of it as much as possible. Otherwise I’d get made fun of for how I carried my books, or walked, or moved my hands and whatever else. When it came to be time for dating, the expectations of the “masculine roles” during courtship and sex didn’t come naturally to me and didn’t bring me pleasure upon completion.

Most of all, I resented the obligation to socialize with guys all the time. I remember hating sports and the way I was always expected to know how each team was doing; if I didn’t know, I was made to feel like a freak. I recall a handful of times where the men in my family or friend-group would make plans to go play basketball or football while the women went shopping and wishing I could go with them instead. The way guys talked about girls and feminine things made me uncomfortable, but if I spoke up in defense of anything “girly” I’d invariably get teased or have my manhood (essentially my status, in those circles) openly questioned. I was disturbed by the constant way men size each other up, compete over the silliest things, and rib each other. I never wanted to act that way, and felt hurt when others would put me in those positions. It made me depressed the way I was expected to be assertive, tough, athletic and chauvinistic at all times.

Chapter 2: Rebellion

As a result of these issues, I always greatly preferred the company of women. Being with them made me feel more relaxed, like I could be myself and didn’t have to follow a script. In middle school, someone even started a rumor about me that I was gay because I hung out with girls but never asked any of them out. In addition, when playing videogames or setting up digital profiles (like on Xbox 360) I used female avatars. (Perhaps it was a form of escape, or experimentation since I couldn’t present as female in real life.) My favorite character in Soul Calibur II was Cassandra, and when playing against guys, they’d tend to laugh about that…until I beat them while using her.

Even with all that uncertainty and shame surrounding my natural inclinations, growing up I always did things that were feminine whenever I found the opportunity. As a little kid I wore my mom’s high heels a few times. She caught me once and said in an amused but firm tone “those aren’t for boys.” As I got older, I’d draw on my nails with pencil or marker to imitate the nail polish I couldn’t have. I remember seeing Happy Feet with some friends when one of the girls in our group playfully put her matching pink hat and scarf on me. The guys in the group were laughing derisively and telling me to take them off, but I didn’t. It made me happy to wear them, and to have the other girls we were with smile and tell me I looked cute.

These little “experiments” came to a head around 13~14, when I found some costume dresses in the basement. I took the dresses up to my room to wear in private, and kept them there for weeks to put on whenever I could. Unfortunately my mom eventually found them and yelled at me for it, and as a result, I never dared try again under her roof. That night I could hear my parents talking about it–my mom was especially angry and at times sounded worried. From my perspective, it felt as if they were discussing what to do about their juvenile-delinquent or cancer-ridden relative. It was as if cross-dressing was the worst fate that ever could have befallen me. I felt absolutely ashamed–if cross-dressing had evoked this kind of reaction, it must be a really horrible thing I’d done. I was scared what they would do or say to me afterwards, but “luckily” it seems my parents decided the best remedy was to pretend it didn’t happen.

At the time I had done these things, I couldn’t explain my situation or long-term intentions. It was just an impulse, a subconscious desire, to be feminine wherever I could. I still didn’t know what “transgender” was, and except for the incident with the dresses, I wasn’t even old enough to equate these feminine actions with my sexuality. (IE, it wasn’t a sexual kink or fetish.) They just made me feel happy and affirmed in the way a baseball player feels after a home run, or a student feels when they graduate. It was, what F Scott Fitzgerald might call a “platonic conception of [myself.]”

Chapter 3: Revelation

It wasn’t until I was around 14~16 (I forget exactly when) that I saw the episode of Law and Order SVU entitled “Fallacy.” That episode dealt with the existence of transgender people, and was the first time I learned two very important facts. First, even if it wasn’t everybody, I at least wasn’t alone in feeling the way I did all the time. Second and most significantly, these other people who felt that way actually did something about it. I’m sure if skeptics or bigots were reading this essay, they’d accuse that episode of “making me trans.” In actuality, the tragic tale of Cheryl Avery only gave a definition to the longing that had already been part of my psychology for as long as I can remember.

In hindsight I constantly wish I could go back in time and convince myself to act on that crucial revelation then and there. Unfortunately, I was scared of my parents’ reaction, and I was already bullied enough in school to where I knew any other excuse to single me out was a death sentence. Plus, the transwoman in the episode goes through hell: her family doesn’t support her, her boyfriend kills himself when he finds out and she gets brutally gang-raped in a male prison. So even though it was a big deal to finally understand what I was, I had no reason to believe anyone would support me and I was scared of what could happen. So, I decided it was best to just try suppressing it. I nit-picked Cheryl’s story for any little reasons why her symptoms were more extreme than mine, and how I therefore “couldn’t possibly” be trans. I kept telling myself I was just an effeminate guy that liked doing a lot of womanly activities.

So I repressed it for a long time. If you read a lot of trans people’s stories, that’s a common occurrence, this cycle of realizations and repressions. Some feel comfortable enough to come out when they’re teens, others not until they’re middle aged or even later. It’s all down to when they’re either in a good enough place to feel safe coming out, or they’ve hit rock bottom and have no other choice but to finally confront the source of their unhappiness. When I finally got my own place in college, as in a full apartment with my own private room, literally the first thing that came to mind was that I finally had a safe area to be myself again. For the first time in almost ten years, I wore dresses and other girl clothes, and for the first time ever I started applying real makeup.

It was coming to the lowest point in my life in late 2014 that really gave me the excuse to finally just go through with it. After admitting to myself how miserable I was, how much of my happiness was fleeting and dependent on others, I ran out of excuses to live the charade any longer. A particularly potent bout of self-reflection around the same time further clarified what I needed to do. I studied my poster of Grace Slick and Janis Joplin. I wanted to look like them, embody the same mixture of sensual beauty with confident inner power. I also contemplated that even if things didn’t work out and I ended up being an unattractive or disadvantaged woman, I’d still prefer that existence to the way I currently was as a man. I’d rather be the lowest, most unfortunate woman than the most successful man.

Chapter 4: Rejuvenation

Even after publicly coming out to everyone, I wanted to wait before presenting female in public for a variety of reasons. I didn’t feel safe going out in a wig, so I decided to let my hair grow out to should-length and for HRT to soften my features first. That ended up taking two years, which coincidentally is also how long it took for me to graduate from college. Those two years were exciting but challenging, as I got to define my feminine persona in private…but still had to go out in guy-mode the rest of the time. This is where I learned how to do makeup (IE don’t put eye shadow up to the eyebrows and don’t put blush on your cheeks) and collected a wardrobe via Amazon. (On one occasion, some girl friends invited me to go out shopping. I was a bit nervous getting dresses while still presenting male at first, but ultimately just owned it and nobody at the store made a fuss.)

It was only after meeting my girlfriend in Spring 2017 that I summoned the courage to go outside as a woman. Even so, I only wanted to do it in the dead of night so my features wouldn’t be too apparent and there wouldn’t be too many people outside. That first experience was terrifying but magical; I recall fearing that any person we crossed paths with would clock me but it never happened. (We got catcalled and honked at though, which was distressing as someone who’d never experienced that behavior before.) It started raining at one point, which I remember perceiving as a bad omen until it stopped just a few minutes later and we saw several bunnies along the way back. (Bunnies are my favorite animal.) That reassured me that the universe approved :P. On subsequent midnight trips we stopped in at 24 hour convenience stores, and the employees gendered me correctly. Needless to say, that was a huge confidence booster as well.

This string of life-affirming successes culminated in my 25th birthday that same year. That was the first time I went out in daytime and alone. It hadn’t been planned; I just saw the way I looked in the mirror and selfies that morning and decided I was passable enough to try. After stepping outside the apartment door, I was terrified and even seriously considered chickening out, but ultimately I knew it had to happen sometime. On the elevator down, a guy got on and I thought for sure he’d clock me. But then he just…never did. I went outside, still apprehensive, and to my immense relief not a single person stared, said anything nasty or treated me differently at all. Even when I crossed some rowdy teenagers on the street, not a single person clocked me. This all sounds so mundane when I write it out years later, but making it over to her apartment undetected by anyone was maybe the most ecstatic I’ve ever felt in my life. It was, and I suspect will always remain, my best birthday ever. In a sense, my first birthday.

And I’ve been living as Cassandra full-time ever since. Coming out as transgender certainly hasn’t solved all my problems with anxiety or success in the real world. But getting to be myself all the time, publicly exist the way I want, openly like what I want to like…well, that certainly helps.

Epilogue: Reaction

I unfortunately lost a lot of friends from High school after coming out of the closet. There was a period where every day I’d notice another 10~20 people had unfriended me on social media until my friends list was maybe half of what it had once been. Only one person I knew well from college (my then-roommate) was a jerk about it. He literally said: “oh no, you’re going through that phase again? Well I’ll set you straight–you’re a MAN!!” I’ve never forgotten that moment because it was so hurtful, especially after all the time I spent comforting him that year when his girlfriend dumped him. At the same time, I got some of the nicest messages I’ve ever received from High school acquaintances I barely knew, even if close friends from those days stopped answering my messages or inviting me to the local get-togethers. You really never know who’s going to be supportive and who isn’t.

For awhile it seemed as though my parents weren’t going to support me. The road was bumpy and took 4 years to overcome, but eventually we reached a point where they got it. They went from thinking that I was dead to realizing it’s my same “essence” just wrapped up in a different package. Some family members reached out to me from the very beginning with support. Others took awhile longer, but ultimately sent reassuring messages too. Just this past month I finally felt safe enough to go to a family wedding, and received a warm welcome from all my relatives including those whom I wasn’t sure would understand. I can’t tell you how great it feels to be accepted as myself, even from people I thought would never come around. It doesn’t always happen, but sometimes people change.

The point is, I was willing to do this with or without their support–amazing as it is to have. And that’s the leap of faith you have to be willing to take if you’re transgender. You have to be willing to put yourself first for a change and live your own life as opposed to trying to please everyone else. It’s scary–coming out to my parents was the most anxiety-inducing decision I ever made–but the alternative is worse. No one should have to live their life repressed and afraid; you are worth fighting for.


  1. Your experiences are beyond anything I’ve ever had to deal with but you fill me with nothing but admiration. I can only hope that if any of my friends had transitioned as you have, or the other way, that I would have been as understanding and supportive as those who helped you. That you can be what you feel yourself to be is the best thing on earth.

    Liked by 1 person

  2. Good story Cassie, helps me understand you even better. Glad you were able to finally become your real self. You are a wonderful woman and great girfriend.


  3. I can’t improve on what mbc1955 says! I would like to add, though, that I’ve learnt a very important lesson from you, namely not to be afraid (or ashamed) of my feminine side. My perspective on life is quite different now. Who would have thought it? Thank you, Cassandra.


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